Sep 22 On This Day: Nathan Hale, 'Brave, Hero, Crappy Spy,' Executed

Two hundred and forty one years ago today, as he faced execution for espionage on behalf of the American colonies, Nathan Hale uttered the immortal line, "I only regret that I have but one life to lose for my country."

Or maybe he didn't. A study by the Library of Congress (LOC) says there's no contemporary evidence he actually said that. But there's little harm in giving what the LOC called the "patron saint of American intelligence" the benefit of the doubt.

Nathan Hale, just 21 years old when he died, was one of America's first spies, operating for George Washington's Continental Army. For all his courage, he was, by most accounts, not well-trained nor particularly good at espionage.

"Brave. Hero. Crappy spy." is how John Sipher, a former member of the CIA’s Senior Intelligence Service, once described Hale.

A declassified CIA historical review said Hale "was an intensely idealistic young man, seized with a burning ardor for independence, and filled with an almost overwhelming desire to perform a signal service for his country."

The CIA review says Hale, a Yale graduate and Army captain, at first blanched at taking on the role of a spy, rather than as a soldier, because spying was not considered honorable. But eventually Hale's urge "to be useful" pushed him in mid-September to volunteer for a daring behind-enemy-lines reconnaissance mission in the New York area to report on British troop sizes and movements.

The details of the mission and precisely what went wrong are not clear, but Hale was reported to have made landfall behind the lines on Sept. 16 under the guise of an unemployed schoolteacher.

But within five days somehow Hale was discovered and apprehended by British forces on Sept. 21. British Gen. William Howe, in apparent reference to Hale, noted in his daybook the next day, "A spy from the Enemy (by his own full confession) apprehended last night, was this day Executed at 11 o'Clock in front of the Artillery Park."

The LOC study said Hale's mission has been doomed from the start. He "was given no secret ink, no code or cypher, nor was he given any training," the study says, citing the writings of former intelligence officer-turned-historian Maj. Gen. E.R. Thompson. Another former intelligence officer-turned-historian, G.J.A. O'Toole, is quoted as saying the "general reason for the failure of [Hale's] mission is obvious -- it was a thoroughly amateurish undertaking in a business that permits few mistakes."

Still, Hale is considered a hero and a martyr for the American intelligence community. A statue of him stands at a place of honor outside CIA headquarters in Langley, Virginia.

"Following Hale’s gallant attempt, our Nation’s fledgling intelligence effort, overseen by George Washington, would grow in sophistication and contribute to America’s victory. Today, Nathan Hale’s statue stands here at CIA as an enduring reminder of the duties and sacrifices inherent to intelligence work," then-CIA Director John Brennan said in a video posted online before July 4, 2015. "Hale's bravery has made him an icon of liberty and patriotism. On this 239th anniversary of American independence, we at CIA pay tribute to him and to all the brave Americans who have served our country, defended our freedoms, and protected our way of life."